Macklemore’s 5 Best Songs Go From Thrift Shops to Protest Anthems

Last September 4 and 5 at MetLife Stadium in New Jersey, rapper Macklemore addressed the genocide live on stage, and it led to him being removed from Ed Sheeran’s The Loop North American Tour. Robert Kraft, the owner of football team the New England Patriots and Gillette Stadium, demanded that he be removed from the tour. Shortly after Macklemore’s removal, other openers followed suit in support of the pro-Palestine struggle, with artists such as Finneas, Lukas Graham, Aaron Rowe, and Sheeran’s backing band Beoga also leaving the tour.

What better time to give him all the support he needs for his awareness and activism towards the Palestinian people during the ongoing genocide? Macklemore’s impact in pop music and politics has become stronger than ever. Throughout his more than a decade-long career as one of hip-hop’s most outspoken rappers to date, here are the five essential Macklemore songs.

Can’t Hold Us (ft. Ray Dalton)

One of the biggest highlights from 2012’s The Heist, “Can’t Hold Us” holds its place as one of Macklemore’s best for its stadium-sized choruses and epic gospel-influenced hook. The song opens with the iconic “It’s the return of the Mack,” establishing the dominance Macklemore, Ryan Lewis, and Ray Dalton had on the pop culture sphere ever since the early 2010s. The real glue that holds this single together is the rapper’s tongue-twister verses and Dalton’s vocal runs that ultimately became his breakthrough track as a solo artist as well. “Can’t Hold Us” stands as one of Macklemore’s unbeatable hits.

Thrift Shop 

Close friends and collaborators Macklemore and Ryan Lewis wouldn’t have reached the top of the pop-rap mountain without “Thrift Shop.” The 2012 Grammy Award-winning breakthrough single for both artists called for a homage to everyone’s favorite pastime: rummaging through second-hand trinkets and “wearing your granddad’s clothes.” The Wanz-assisted chorus singing about being “fucking awesome” is still 14 years later.

Good Old Days (ft. Kesha)

In the calmer and more intimate cuts from his discography, Macklemore invites electropop artist Kesha for “Good Old Days.” Showcasing his more honest and retrospective side, one of the biggest highlights was Kesha’s strong vocals and the string section that builds throughout the song. “You’ll miss the magic of those good old days,” Kesha sings in a more compelling delivery about how growing up is inevitable. This song in particular is one of Macklemore’s more successful collaborations; effective in terms of exchanging hooks and verses seamlessly.  

Downtown (ft. Melle Mel, Grandmaster Caz, Kool Moe Dee, Eric Nally)

In 2016’s This Unruly Mess I’ve Made, one of the album’s biggest hits is “Downtown,” an unhinged glam rock, classic hip-hop, and big band fusion of a chaotic mess. What starts as a basic piano rhythm with Macklemore playing around with syllables about becoming cool, while Grandmaster and the Furious Five’s Melle Mel, Grandmaster Caz, and Kool Moe Dee finesse their way with their harmonious rap delivery, in comes Eric Nally’s Freddie Mercury yelps that skyrocket the track’s energy to an 11. “Downtown” is a ridiculous mixture of genre styles that works so well together. 

Hind’s Hall

Macklemore’s “Hind’s Hall” was inspired by the Columbia University pro-Palestine protests back in 2024. Here, Macklemore raps about the ongoing genocide happening in Gaza, where multiple civilians have been targeted by the Israeli Defense Forces. While this song lacks a chorus, the message is what matters, and it has become more powerful than Macklemore’s previous releases. If anything, the message is already clear when Macklemore pays homage to N.W.A. in the first verse with “When I was seven, I learned a lesson from Cube and Eazy-E/ What was it again? Oh yeah, fuck the police.”

Elijah Pareño

Music Writer

Elijah Pareño is the Music Writer of Rolling Stone Philippines. He writes daily music news, features, reviews, and radar stories of the website.

In addition to music writing, Pareño has written about the behind-the-scenes writers and producers from the P-pop scene, interviewed hip-hop artists like Shanti Dope and Zae, and featured up-and-coming artists for the Music Forecast 2026. Aside from music, Pareño has written about the state of affairs that affects pop culture. He wrote a movie review for 'Mortal Kombat II' and reported and interviewed photojournalists at the September 21, 2025 protests in Luneta and Mendiola.

Prior to working in Rolling Stone Philippines, Pareño was a freelance writer for 3 years and independent live music promoter

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